US4895880A - Photocurable compositions containing photobleachable ionic dye complexes - Google Patents

Photocurable compositions containing photobleachable ionic dye complexes Download PDF

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Publication number
US4895880A
US4895880A US07/098,358 US9835887A US4895880A US 4895880 A US4895880 A US 4895880A US 9835887 A US9835887 A US 9835887A US 4895880 A US4895880 A US 4895880A
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United States
Prior art keywords
dye
composition
photohardenable composition
compound
counter ion
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Expired - Lifetime
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US07/098,358
Inventor
Peter Gottschalk
Douglas C. Neckers
Gary B. Schuster
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Eastman Kodak Co
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Mead Corp
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Priority to US86036786A priority Critical
Application filed by Mead Corp filed Critical Mead Corp
Assigned to MEAD CORPORATION, THE, COURTHOUSE PLAZA NE, DAYTON, OHIO 45463 A CORP. OF OHIO reassignment MEAD CORPORATION, THE, COURTHOUSE PLAZA NE, DAYTON, OHIO 45463 A CORP. OF OHIO ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: GOTTSCHALK, PETER
Priority to US07/098,358 priority patent/US4895880A/en
Publication of US4895880A publication Critical patent/US4895880A/en
Application granted granted Critical
Assigned to CYCOLOR IMAGING, INC. reassignment CYCOLOR IMAGING, INC. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: MEAD CORPORATION, THE
Assigned to EASTMAN KODAK reassignment EASTMAN KODAK ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CYCOLOR INC.
Anticipated expiration legal-status Critical
Assigned to CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT reassignment CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT FIRST LIEN OF INTELLECTUAL PROPERTY SECURITY AGREEMENT Assignors: CARESTREAM HEALTH, INC.
Assigned to CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT reassignment CREDIT SUISSE, CAYMAN ISLANDS BRANCH, AS ADMINISTRATIVE AGENT SECOND LIEN INTELLECTUAL PROPERTY SECURITY AGREEME Assignors: CARESTREAM HEALTH, INC.
Assigned to CARESTREAM HEALTH, INC. reassignment CARESTREAM HEALTH, INC. RELEASE OF SECURITY INTEREST IN INTELLECTUAL PROPERTY (FIRST LIEN) Assignors: CREDIT SUISSE AG, CAYMAN ISLANDS BRANCH
Application status is Expired - Lifetime legal-status Critical

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Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08FMACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00Processes of polymerisation
    • C08F2/46Polymerisation initiated by wave energy or particle radiation
    • C08F2/48Polymerisation initiated by wave energy or particle radiation by ultra-violet or visible light
    • C08F2/50Polymerisation initiated by wave energy or particle radiation by ultra-violet or visible light with sensitising agents
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/002Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor using materials containing microcapsules; Preparing or processing such materials, e.g. by pressure; Devices or apparatus specially designed therefor
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/029Inorganic compounds; Onium compounds; Organic compounds having hetero atoms other than oxygen, nitrogen or sulfur
    • GPHYSICS
    • G03PHOTOGRAPHY; CINEMATOGRAPHY; ELECTROGRAPHY; HOLOGRAPHY
    • G03FPHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
    • G03F7/00Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
    • G03F7/004Photosensitive materials
    • G03F7/027Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
    • G03F7/028Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
    • G03F7/031Organic compounds not covered by group G03F7/029
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/114Initiator containing
    • Y10S430/115Cationic or anionic
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/114Initiator containing
    • Y10S430/117Free radical
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S430/00Radiation imagery chemistry: process, composition, or product thereof
    • Y10S430/1053Imaging affecting physical property or radiation sensitive material, or producing nonplanar or printing surface - process, composition, or product: radiation sensitive composition or product or process of making binder containing
    • Y10S430/1055Radiation sensitive composition or product or process of making
    • Y10S430/128Radiation-activated cross-linking agent containing

Abstract

A process for coating a substrate with an essentially colorless radiation curable composition which comprises coating said substrate with a visible light sensitive composition comprising a free radical addition polymerizable or crosslinkable material and a photobleachable ionic dye-counter ion compound capable of absorbing visible light and generating free radicals; exposing said composition to light to harden said composition; and bleaching said composition to an essentially colorless state, and photohardenable compositions containing photobleachable ionic dye-counter ion compounds as photoinitiators useful in the aforesaid process.

Description

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a continuation-in-part of U.S. application Ser. No. 944,305, filed Dec. 18, 1986 which in turn is a continuation-in-part of Ser. No. 860,367, filed May 6, 1986, abandoned, which is a continuation-in-part of Ser. No. 800,014, filed Nov. 20, 1985, abandoned.

BACKGROUND OF THE INVENTION

The aforementioned related application, which corresponds to European Application Publication No. 0233587, relates to photocurable compositions containing ionic dye complexes as photoinitiators. These complexes are characterized in that they directly or indirectly yield free radicals upon exposure to actinic radiation and particularly visible light.

By nature, compositions which are sensitive to visible light appear colored to the human eye. There are applications in which it would be desirable to use the compositions which can be cured upon exposure to visible light but for the colored appearance of these compositions. For example, in laminating glass, if the composition is colored it imparts a tint to the glass which may be undesirable. Similarly, a visible initiator would be advantageous in coating optical fibers but for its colored appearance. In these applications, photobleachable ionic dye complexes would be particularly useful. In some of the compositions disclosed in the related application, the dye has been observed to be photobleachable.

SUMMARY OF THE INVENTION

The present invention particularly relates to visible light sensitive photocurable compositions containing a photobleachable ionic dye complex as an initiator.

Another manifestation of the present invention is a process for coating a substrate with a visible light curable composition wherein the process is characterized in that the composition contains a photobleachable ionic dye complex as a photoinitiator.

The compositions and process of the present invention are useful in applications in which essentially colorless (e.g., clear, transparent or white) radiation cured coatings are desired. Typical examples of such applications are in laminating glass, coating optical fibers or in coating compositions containing white pigments such as titanium dioxide.

DETAILED DESCRIPTION OF THE INVENTION

The ionic dye complexes used in the present invention are generally described in U.S. Pat. No. 4,772,530. Xanthane dye complexes are more particularly described in commonly assigned U.S. application Ser. No. 057,544, filed June 3, 1987.

The ionic dye complexes used in the present invention are characterized in that they are photobleachable.

The polymerizable or crosslinkable materials described in the aforementioned applications are useful herein. The photoinitiator systems described in the aforementioned applications are also useful herein with the requirement that the ionic dye-counter ion compounds be photobleachable. Of the dye complexes disclosed in U.S. application Ser. No. 944,305 corresponding to European Application Publication No. 0233587, all of the cyanine dye complexes are photobleachable with varying efficiency and speed. Some of the more efficient photobleachable complexes are: ##STR1## The azine dye complex of Methylene Blue and triphenylbutylborate is one of the most efficient complexes in terms of photobleachability. Its structure is ##STR2## Rose Bengal-onium dye complexes are also photobleachable. Of these complexes of Rose Bengal and its benzylester with diphenyliodonium ions (including di(4-t-butylphenyl)iodonium ions) are photobleachable with high efficiency.

Herein, the photobleachable dye complexes may bleach upon exposure to visible light upon curing the compositions, or they may be bleached upon post-exposure to a bleaching radiation such as ultraviolet radiation.

Having described the invention in detail and by reference to preferred embodiments thereof, it will be apparent that modifications and variations are possible without departing from the scope of the invention defined in the appended claims.

Claims (19)

What is claimed is:
1. A visible-light sensitive photohardenable composition comprising a free radical addition polymerizable or crosslinkable material and a photobleachable ionic dye-counter ion compound, said compound being capable of absorbing visible light and producing free radicals which initiate polymerization or crosslinking of said material.
2. The photohardenable composition of claim 1 wherein prior to exposure, said ionic dye-counter ion compound is a stable, non-transient compound.
3. The photohardenable composition of claim 1 wherein said ionic dye-counter ion compound is soluble in said free radical addition polymerizable or crosslinked compound.
4. The photohardenable composition of claim 3 wherein following exposure of said ionic dye-counter ion compound to light, an electron is transferred from said dye to said counter ion or from said counter ion to said dye and the rate of said electron transfer is greater than a diffusion controlled rate.
5. The photohardenable composition of claim 1 wherein said compound is an anionic dye compound.
6. The photohardenable composition of claim 5 wherein said anionic dye is selected from the group consisting of xanthene and oxonol dyes.
7. The photohardenable composition of claim 6 wherein said ionic dye counter ion compound is an anionic dye-onium ion complex or an anionic dye-pyryllium ion complex.
8. The photohardenable composition of claim 7 wherein said dye is a xanthene dye.
9. The photohardenable composition of claim 1 wherein said ionic dye counter ion compound is a cationic dye-borate anion compound represented by the formula (I): ##STR3## where D is a cationic dye moiety; and R1, R2, R3 and R4 are the same or different and selected from the group consisting of alkyl, aryl, aralkyl, alkaryl, alkenyl, alkynyl, alicyclic, heterocyclic, and allyl groups.
10. The photohardenable composition of claim 9 wherein said cationic dye is selected from the group consisting of cationic methine, polymethine, triarylmethane, indoline, azine, thiazine, xanthene, oxazine, and acridine dyes.
11. The photohardenable composition of claim 10 wherein said cationic dye is selected from the group consisting of cationic cyanine, carbocyanine, hemicyanine, rhodamine, and azamethine dyes.
12. The photohardenable composition of claim 11 wherein said polymerizable or crosslinkable material contains an ethylenically unsaturated compound.
13. The photohardenable composition of claim 12 wherein at least one of R1, R2, R3 and R4 is an alkyl group.
14. The photohardenable composition of claim 13 wherein R1, R2, and R3 are aryl groups and R4 is an alkyl group.
15. The photohardenable composition of claim 7 wherein said photobleachable ionic dye-counter ion compound is a complex of Rose Bengal or Rose Bengal benzyl ester with a diphyliodonium ions.
16. The photohardenable composition of claim 9 wherein said cationic dye is an azine dye.
17. The photohardenable composition of claim 16 wherein said azine dye is Methylene Blue.
18. The photohardenable composition of claim 16 wherein said cationic dye is selected from the group consisting of ##STR4##
19. A process for coating a substrate with an essentially colorless radiation curable composition which comprises coating said substrate with a visible light sensitive composition comprising a free radical addition polymerizable or crosslinkable material and a photobleachable ionic dye-counter ion compound capable of absorbing visible light and generating free radicals; exposing said composition to light to harden said composition; and bleaching said ionic dye to an essentially colorless state.
US07/098,358 1986-05-06 1987-09-18 Photocurable compositions containing photobleachable ionic dye complexes Expired - Lifetime US4895880A (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US86036786A true 1986-05-06 1986-05-06
US07/098,358 US4895880A (en) 1986-05-06 1987-09-18 Photocurable compositions containing photobleachable ionic dye complexes

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US07/098,358 US4895880A (en) 1986-05-06 1987-09-18 Photocurable compositions containing photobleachable ionic dye complexes
JP23214688A JPH01152450A (en) 1987-09-18 1988-09-16 Photocurable composition containing photobleachable ion dye complex
CN88106711A CN1032807A (en) 1987-09-18 1988-09-16 Photocurable compositions containing photobleachable ionic dye complexes
DE19883851191 DE3851191T2 (en) 1987-09-18 1988-09-19 A process for coating a substrate.
EP88308663A EP0308274B1 (en) 1987-09-18 1988-09-19 Process for coating a substrate
DE19883851191 DE3851191D1 (en) 1987-09-18 1988-09-19 A process for coating a substrate.

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US06/944,305 Continuation-In-Part US4772530A (en) 1986-05-06 1986-12-18 Photosensitive materials containing ionic dye compounds as initiators

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EP (1) EP0308274B1 (en)
JP (1) JPH01152450A (en)
CN (1) CN1032807A (en)
DE (2) DE3851191D1 (en)

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US5262276A (en) * 1988-05-11 1993-11-16 Fuji Photo Film Co., Ltd. Light-sensitive compositions
US5616443A (en) 1993-08-05 1997-04-01 Kimberly-Clark Corporation Substrate having a mutable colored composition thereon
US5643356A (en) 1993-08-05 1997-07-01 Kimberly-Clark Corporation Ink for ink jet printers
US5645964A (en) 1993-08-05 1997-07-08 Kimberly-Clark Corporation Digital information recording media and method of using same
US5681380A (en) 1995-06-05 1997-10-28 Kimberly-Clark Worldwide, Inc. Ink for ink jet printers
US5686503A (en) 1994-06-30 1997-11-11 Kimberly-Clark Corporation Method of generating a reactive species and applications therefor
US5700850A (en) 1993-08-05 1997-12-23 Kimberly-Clark Worldwide Colorant compositions and colorant stabilizers
US5721287A (en) 1993-08-05 1998-02-24 Kimberly-Clark Worldwide, Inc. Method of mutating a colorant by irradiation
US5733693A (en) 1993-08-05 1998-03-31 Kimberly-Clark Worldwide, Inc. Method for improving the readability of data processing forms
US5739175A (en) 1995-06-05 1998-04-14 Kimberly-Clark Worldwide, Inc. Photoreactor composition containing an arylketoalkene wavelength-specific sensitizer
US5747550A (en) 1995-06-05 1998-05-05 Kimberly-Clark Worldwide, Inc. Method of generating a reactive species and polymerizing an unsaturated polymerizable material
US5773182A (en) 1993-08-05 1998-06-30 Kimberly-Clark Worldwide, Inc. Method of light stabilizing a colorant
US5782963A (en) 1996-03-29 1998-07-21 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
US5786132A (en) 1995-06-05 1998-07-28 Kimberly-Clark Corporation Pre-dyes, mutable dye compositions, and methods of developing a color
US5798015A (en) 1995-06-05 1998-08-25 Kimberly-Clark Worldwide, Inc. Method of laminating a structure with adhesive containing a photoreactor composition
US5811199A (en) 1995-06-05 1998-09-22 Kimberly-Clark Worldwide, Inc. Adhesive compositions containing a photoreactor composition
US5837429A (en) 1995-06-05 1998-11-17 Kimberly-Clark Worldwide Pre-dyes, pre-dye compositions, and methods of developing a color
US5849411A (en) 1995-06-05 1998-12-15 Kimberly-Clark Worldwide, Inc. Polymer film, nonwoven web and fibers containing a photoreactor composition
US5855655A (en) 1996-03-29 1999-01-05 Kimberly-Clark Worldwide, Inc. Colorant stabilizers
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US6008268A (en) 1994-10-21 1999-12-28 Kimberly-Clark Worldwide, Inc. Photoreactor composition, method of generating a reactive species, and applications therefor
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US6486227B2 (en) 2000-06-19 2002-11-26 Kimberly-Clark Worldwide, Inc. Zinc-complex photoinitiators and applications therefor
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JPH03163106A (en) * 1989-06-30 1991-07-15 Mead Corp:The Cationic polymerizable composition containing photopolymerization initiator comprising ionic dye-reactive counter ion complex and onium salt, and photosensitive material prepared therefrom
US6207359B1 (en) 2000-02-22 2001-03-27 Eastman Kodak Company Method for reducing the dye stain in photographic elements
US6376163B1 (en) 2000-02-22 2002-04-23 Eastman Kodak Company Photobleachable composition, photographic element containing the composition and photobleachable method

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Cited By (60)

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US5262276A (en) * 1988-05-11 1993-11-16 Fuji Photo Film Co., Ltd. Light-sensitive compositions
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JPH01152450A (en) 1989-06-14
DE3851191T2 (en) 1995-01-19
EP0308274B1 (en) 1994-08-24
CN1032807A (en) 1989-05-10
EP0308274A2 (en) 1989-03-22
EP0308274A3 (en) 1989-07-12
DE3851191D1 (en) 1994-09-29

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